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四齿蟾蜍毒素 Tb-210B、Tb-226、Tb-242C 和 Tb-258 的生物合成中间体的全合成。

Total Syntheses of the Proposed Biosynthetic Intermediates of Tetrodotoxin Tb-210B, Tb-226, Tb-242C, and Tb-258.

机构信息

Graduate School of Bioagricultural Sciences, Nagoya University, Furo-cho, Chikusa-ku, Nagoya 464-8601, Japan.

Graduate School of Pharmaceutical Sciences, Tohoku University, 6-3 Aoba, Aramaki, Aoba-ku, Sendai 980-8578, Japan.

出版信息

J Org Chem. 2022 Jul 15;87(14):9023-9033. doi: 10.1021/acs.joc.2c00704. Epub 2022 Jun 28.

Abstract

The collective synthesis of the four -cyclic guanidines Tb-210B, Tb-226, Tb-242C, and Tb-258, all of which have been isolated from puffer fish and are considered possible biosynthetic intermediates of tetrodotoxin, has been achieved. Our synthesis is based on the stepwise deoxygenation or hydroxylation of a common intermediate, prepared from a known oxazoline.

摘要

已成功实现了从河豚鱼中分离出的四种四环胍类化合物 Tb-210B、Tb-226、Tb-242C 和 Tb-258 的集体合成,这些化合物都被认为是河豚毒素可能的生物合成中间体。我们的合成是基于从已知恶唑啉制备的共同中间体的逐步脱氧或羟化。

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